3-[2-(3,4-dimethoxyphenyl)-2-oxo-ethyl]isobenzofuran-1(3H)-one | 55377-46-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[2-(3,4-dimethoxyphenyl)-2-oxo-ethyl]isobenzofuran-1(3H)-one
• 英文别名: 3-[2-(3,4-dimethoxy-phenyl)-2-oxo-ethyl]-3H-isobenzofuran-1-one；3,4-Dimethoxyphenacylphthalid；3-[2-(3,4-dimethoxyphenyl)-2-oxoethyl]-2-benzofuran-1(3H)-one；3-[2-(3,4-dimethoxyphenyl)-2-oxoethyl]-3H-2-benzofuran-1-one
• CAS: 55377-46-3
• 化学式: C₁₈H₁₆O₅
• 分子量: 312.322
• InChiKey: ZBHXTOAOZYOSCO-UHFFFAOYSA-N

物化性质

• 沸点：
  506.8±50.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-[2-(3,4-dimethoxyphenyl)-2-oxo-ethyl]isobenzofuran-1(3H)-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以87%的产率得到3-[2-(3,4-dimethoxyphenyl)-2-hydroxyethyl]-3H-2-benzofuran-1-one
  参考文献：
  名称：

  Convenient Synthesis of 3-Styrylphthalides

  摘要：

  A convenient, high yield, two-step method is described for 3-styrylphthalides ( 3a - e) from 3-phenacylphthalides ( 1a - e).

  DOI：

  10.1080/00397919708003050
• 作为产物：
  描述：

  邻羧基苯甲醛 、 3,4-二甲氧基苯乙酮 在 1-methyl-3-(propyl-3-sulfonic acid)imidazolium triflate supported on magnetic nanoparticles 作用下， 以 neat (no solvent) 为溶剂， 反应 0.2h， 以90%的产率得到3-[2-(3,4-dimethoxyphenyl)-2-oxo-ethyl]isobenzofuran-1(3H)-one
  参考文献：
  名称：

  1-Methyl-3-(propyl-3-sulfonic acid)imidazolium triflate supported on magnetic nanoparticles: an efficient and reusable catalyst for synthesis of mono- and bis-isobenzofuran-1(3H)-ones under solvent-free conditions

  摘要：

  在无溶剂热条件和微波辐射下，报道了一种高度可回收的催化剂[HSO3PMIM]OTf–SiO2@MNPs存在下合成异苯并呋喃-1(3H)-酮衍生物的高效程序。

  DOI：

  10.1039/c4ra14112a

文献信息

• Benzofuranones as potential antinociceptive agents: Structure–activity relationships
  作者：Cleiton José Gonçalves、Andrey Sávio Lenoir、Pâmela Padaratz、Rogério Corrêa、Rivaldo Niero、Valdir Cechinel-Filho、Fátima de Campos Buzzi

  DOI：10.1016/j.ejmech.2012.08.015

  日期：2012.10

  This work evaluates the antinociceptive properties of benzofuranones using chemically induced models of pain and the hot plate test. All the compounds exhibited significant antinociceptive activity, with 3-[2-(4-chlorophenyl)-2-oxoetil]-2-benzofuran-1(3H)-one (3d) being the most active. According to the application of the Topliss method, the 2 pi-pi(2) parameter was the preponderant one, indicating that the hydrophobicity (pi) seems to be more involved in the antinociceptive activity. Based on the table of other possible substituents proposed by Topliss, three derived from compound 3d were tested. 3-[2-(3-methoxyphenyl)-2-oxoetil]-2-benzofuran-1(3H)-one (3g) showed greater antinociceptive activity with better pharmacokinetic properties predicted. These results show the efficiency of the Topliss Method as a research tool for the discovery of potential candidate molecules for a new antinociceptive drug. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Chatterjea,J.N. et al., Journal of the Indian Chemical Society, 1974, vol. 51, p. 757 - 762
  作者：Chatterjea,J.N. et al.

  DOI：——

  日期：——
• 1-Methyl-3-(propyl-3-sulfonic acid)imidazolium triflate supported on magnetic nanoparticles: an efficient and reusable catalyst for synthesis of mono- and bis-isobenzofuran-1(3H)-ones under solvent-free conditions
  作者：Forouz Rastegari、Iraj Mohammadpoor-Baltork、Ahmad R. Khosropour、Shahram Tangestaninejad、Valiollah Mirkhani、Majid Moghadam

  DOI：10.1039/c4ra14112a

  日期：——

  An efficient procedure for the synthesis of isobenzofuran-1(3H)-one derivatives in the presence of [HSO₃PMIM]OTf–SiO₂@MNPs as a highly recyclable catalyst under solvent-free thermal conditions and MW irradiation is reported.

  在无溶剂热条件和微波辐射下，报道了一种高度可回收的催化剂[HSO3PMIM]OTf–SiO2@MNPs存在下合成异苯并呋喃-1(3H)-酮衍生物的高效程序。
• Convenient Synthesis of 3-Styrylphthalides
  作者：R. S. Mali、Archna Patience Massey

  DOI：10.1080/00397919708003050

  日期：1997.3

  A convenient, high yield, two-step method is described for 3-styrylphthalides ( 3a - e) from 3-phenacylphthalides ( 1a - e).